Phosphorus oxychloride → HCID 178492805, compound

HRID 710542Notes

Reaction equation

HRID 710542 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH2:14][C:15](O)=O)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]([NH:29][NH2:30])=O)=[CH:26][C:21]=2[NH:20][CH:19]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1.O=P(Cl)(Cl)Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH2:14][C:15]2[S:40][C:27]([C:25]3[CH:24]=[CH:23][C:22]4[NH:18][CH:19]=[N:20][C:21]=4[CH:26]=3)=[N:29][N:30]=2)(=[O:12])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 87949Lawesson's reagentHCID 166371191H-benzimidazole-5-carbohydrazideHCID 18790173HCID 18790173, compound

Product 1

HCID 178492805HCID 178492805, compound

Procedure

The compound was synthesized starting from (3,4-dimethoxyphenylsulfonyl)acetic acid (261 mg; 1 mmol), benzimidazol-5-carbohydrazide (176 mg; 1 mmol), Lawesson's reagent (606 mg; 1.5 mmol) and POCl3 (0.137 ml; 1.5 mmol) as described in method 3 but purified by flash chromatography on silica using a CHCl3/MeOH gradient; yield: 0.026 g (6.3%); MS m/z: 417.2 [M+H]hu +; 1H-NMR (DMSO d6, 400 MHz): δ 3.76 (s, 3H); 3.81 (s, 3H); 5.38 (s, 2H); 7.13 (d, 1H3J=8.7 Hz); 7.30 (d, 1H, 4J=2.1 Hz); 7.36 (dd, 1H, 4J=2.1 Hz, 3J=8.7 Hz); 7.69-7.71 (m, 1H); 7.78-7.80 (m, 1H); 8.16 (br s, 1H); 8.35 (s, 1H); 12.76 (br s, 1H); HPLC (METHOD [A]): rt 10.63 min (97.8%)

Workup

  1. customThe compound was synthesized
  2. custompurified by flash chromatography on silica using a CHCl3/MeOH gradient
  3. customrt 10.63 min (97.8%)

Sources & evidence

ORD record
ord-0ef8474ffef045358d6235ecdd0e1b63
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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